Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus

Xiancui Li, Sergey Dobretsov, Ying Xu, Xiang Xiao, Oi Hung, Pei Yuan Qian

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

Modern antifouling coatings use heavy metals and toxic organic molecules to prevent biofouling, the undesirable growth of marine organisms on man-made substrata. In an ongoing survey of deep-sea microorganisms aimed at finding low toxic antifouling metabolites, an actinomycete bacterium was isolated from the Pacific sediment at the depth of about 5000 m. The bacterium was closely related to Streptomyces fungicidicus (99% similarity) according to 16S ribosomal RNA sequence information. The spent culture medium of this bacterium inhibited barnacle larval attachment. Bioassay-guided fractionation was employed to isolate antifouling compounds. The ethyl acetate extract was fractionated by using an open silica gel column. Active fractions were further purified on a HPLC C 18 column. Five diketopiperazines, cyclo-(L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-L-Pro), cyclo-(L-Trp-L-Pro), and cyclo-(L-Leu-L-Val) were isolated for the first time from a deep sea bacterium, and the structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and mass spectrometry. The pure diketopiperazines were tested for antilarval activity using the barnacle Balanus amphitrite . Effective concentrations that inhibited 50% larval attachment (EC 50 ) after 24 h ranged from 0.10 - 0.27 mM. The data suggest that diketopiperazines and other compounds from deep-sea bacteria may be used as novel antifoulants.

Original languageEnglish
Pages (from-to)201-208
Number of pages8
JournalBiofouling
Volume22
Issue number3
DOIs
Publication statusPublished - Jan 1 2006

Fingerprint

Streptomyces fungicidicus
Diketopiperazines
diketopiperazines
antifouling
Streptomyces
Oceans and Seas
deep sea
Thoracica
Bacteria
bacterium
bacteria
Poisons
Cirripedia
Biofouling
antifouling agents
16S Ribosomal RNA
Balanus amphitrite
biofouling
Aquatic Organisms
Actinobacteria

Keywords

  • Antifouling products
  • Deep-sea bacteria
  • Diketopiperazines
  • Streptomyces fungicidicus

ASJC Scopus subject areas

  • Aquatic Science
  • Biotechnology

Cite this

Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus. / Li, Xiancui; Dobretsov, Sergey; Xu, Ying; Xiao, Xiang; Hung, Oi; Qian, Pei Yuan.

In: Biofouling, Vol. 22, No. 3, 01.01.2006, p. 201-208.

Research output: Contribution to journalArticle

Li, Xiancui ; Dobretsov, Sergey ; Xu, Ying ; Xiao, Xiang ; Hung, Oi ; Qian, Pei Yuan. / Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus. In: Biofouling. 2006 ; Vol. 22, No. 3. pp. 201-208.
@article{d8e01bef5d9947278c5d0dc26a729d2e,
title = "Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus",
abstract = "Modern antifouling coatings use heavy metals and toxic organic molecules to prevent biofouling, the undesirable growth of marine organisms on man-made substrata. In an ongoing survey of deep-sea microorganisms aimed at finding low toxic antifouling metabolites, an actinomycete bacterium was isolated from the Pacific sediment at the depth of about 5000 m. The bacterium was closely related to Streptomyces fungicidicus (99{\%} similarity) according to 16S ribosomal RNA sequence information. The spent culture medium of this bacterium inhibited barnacle larval attachment. Bioassay-guided fractionation was employed to isolate antifouling compounds. The ethyl acetate extract was fractionated by using an open silica gel column. Active fractions were further purified on a HPLC C 18 column. Five diketopiperazines, cyclo-(L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-L-Pro), cyclo-(L-Trp-L-Pro), and cyclo-(L-Leu-L-Val) were isolated for the first time from a deep sea bacterium, and the structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and mass spectrometry. The pure diketopiperazines were tested for antilarval activity using the barnacle Balanus amphitrite . Effective concentrations that inhibited 50{\%} larval attachment (EC 50 ) after 24 h ranged from 0.10 - 0.27 mM. The data suggest that diketopiperazines and other compounds from deep-sea bacteria may be used as novel antifoulants.",
keywords = "Antifouling products, Deep-sea bacteria, Diketopiperazines, Streptomyces fungicidicus",
author = "Xiancui Li and Sergey Dobretsov and Ying Xu and Xiang Xiao and Oi Hung and Qian, {Pei Yuan}",
year = "2006",
month = "1",
day = "1",
doi = "10.1080/08927010600780771",
language = "English",
volume = "22",
pages = "201--208",
journal = "Biofouling",
issn = "0892-7014",
publisher = "Taylor and Francis Ltd.",
number = "3",

}

TY - JOUR

T1 - Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus

AU - Li, Xiancui

AU - Dobretsov, Sergey

AU - Xu, Ying

AU - Xiao, Xiang

AU - Hung, Oi

AU - Qian, Pei Yuan

PY - 2006/1/1

Y1 - 2006/1/1

N2 - Modern antifouling coatings use heavy metals and toxic organic molecules to prevent biofouling, the undesirable growth of marine organisms on man-made substrata. In an ongoing survey of deep-sea microorganisms aimed at finding low toxic antifouling metabolites, an actinomycete bacterium was isolated from the Pacific sediment at the depth of about 5000 m. The bacterium was closely related to Streptomyces fungicidicus (99% similarity) according to 16S ribosomal RNA sequence information. The spent culture medium of this bacterium inhibited barnacle larval attachment. Bioassay-guided fractionation was employed to isolate antifouling compounds. The ethyl acetate extract was fractionated by using an open silica gel column. Active fractions were further purified on a HPLC C 18 column. Five diketopiperazines, cyclo-(L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-L-Pro), cyclo-(L-Trp-L-Pro), and cyclo-(L-Leu-L-Val) were isolated for the first time from a deep sea bacterium, and the structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and mass spectrometry. The pure diketopiperazines were tested for antilarval activity using the barnacle Balanus amphitrite . Effective concentrations that inhibited 50% larval attachment (EC 50 ) after 24 h ranged from 0.10 - 0.27 mM. The data suggest that diketopiperazines and other compounds from deep-sea bacteria may be used as novel antifoulants.

AB - Modern antifouling coatings use heavy metals and toxic organic molecules to prevent biofouling, the undesirable growth of marine organisms on man-made substrata. In an ongoing survey of deep-sea microorganisms aimed at finding low toxic antifouling metabolites, an actinomycete bacterium was isolated from the Pacific sediment at the depth of about 5000 m. The bacterium was closely related to Streptomyces fungicidicus (99% similarity) according to 16S ribosomal RNA sequence information. The spent culture medium of this bacterium inhibited barnacle larval attachment. Bioassay-guided fractionation was employed to isolate antifouling compounds. The ethyl acetate extract was fractionated by using an open silica gel column. Active fractions were further purified on a HPLC C 18 column. Five diketopiperazines, cyclo-(L-Leu-L-Pro), cyclo-(L-Phe-L-Pro), cyclo-(L-Val-L-Pro), cyclo-(L-Trp-L-Pro), and cyclo-(L-Leu-L-Val) were isolated for the first time from a deep sea bacterium, and the structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and mass spectrometry. The pure diketopiperazines were tested for antilarval activity using the barnacle Balanus amphitrite . Effective concentrations that inhibited 50% larval attachment (EC 50 ) after 24 h ranged from 0.10 - 0.27 mM. The data suggest that diketopiperazines and other compounds from deep-sea bacteria may be used as novel antifoulants.

KW - Antifouling products

KW - Deep-sea bacteria

KW - Diketopiperazines

KW - Streptomyces fungicidicus

UR - http://www.scopus.com/inward/record.url?scp=33746795061&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746795061&partnerID=8YFLogxK

U2 - 10.1080/08927010600780771

DO - 10.1080/08927010600780771

M3 - Article

C2 - 17290864

AN - SCOPUS:33746795061

VL - 22

SP - 201

EP - 208

JO - Biofouling

JF - Biofouling

SN - 0892-7014

IS - 3

ER -